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Multicomponent reaction derived small di- and tri-carbohydrate-based glycomimetics as tools for probing lectin specificity

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Abstract

Lectins, carbohydrate-binding proteins, play important functions in all forms of life from bacteria and viruses to plants, animals, and humans, participating in cell–cell communication and pathogen binding. In an attempt to modify lectin functions, artificial lectin ligands were made usually as big dendrimeric or cluster multivalent glycomimetic structures. Here we synthesized a novel set of glycomimetic ligands through protection/deprotection multicomponent reactions (MCR) approach. Multivalent di-and tri-carbohydrate glycomimetics containing d-fructose, d-galactose, and d-allose moieties were prepared in 63–96% yield. MCR glycomimetics demonstrated different binding abilities for plant lectins Con A and UEA I, and human galectin-3. Information gained about the influence of molecule structure, multivalency and optical purity on the lectin binding ability can be used in lectin detection and sensitivity measurements to further facilitate understanding of carbohydrate recognition process.

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Acknowledgements

We are grateful for financial support by the Croatian Science Foundation grant number 3102 to I.J. The authors thank Mrs. Milica Perc for excellent technical assistance.

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  1. Division of Organic Chemistry and Biochemistry, Rudjer Bošković Institute, Bijenička c. 54, Zagreb, 10000, Croatia

    Andreja Jakas & Ivanka Jerić

  2. Department of Chemistry and Biochemistry, Florida Atlantic University, 777 Glades Rd., Boca Raton, FL, 33431, USA

    Ramya Ayyalasomayajula & Mare Cudic

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Conceptualization, A.J.; Formal analysis, A.J. R.A.; Investigation, A.J. R.A., M.C.; Methodology, A.J., R.A., I.J., M.C.; Writing–review & editing, A.J., M.C, I.J.

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Correspondence to Andreja Jakas or Ivanka Jerić.

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Jakas, A., Ayyalasomayajula, R., Cudic, M. et al. Multicomponent reaction derived small di- and tri-carbohydrate-based glycomimetics as tools for probing lectin specificity. Glycoconj J 39, 587–597 (2022). https://doi.org/10.1007/s10719-022-10079-3

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